Windermere Oaks
Homes for Sale in Windermere, FL

Windermere Oaks sits within the Town of Windermere in Orange County, an area known more for its chain-of-lakes geography and low-density feel than for large amenitized subdivisions. Current MLS data shows no distinct community amenities tied to this name, which points to a smaller or more residential-only footprint rather than a resort-style development.

Stellar MLS sales records identify 8 homes in Windermere Oaks that have changed hands since 2012, built between 1982 and 2000 (median 1987), with a median living area of about 3,525 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.

Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.

Windermere Oaks is too small for its own price trend, so here is the market around it.

In ZIP 34786, 336 homes are on the market and 26% are under contract — a steady corner of Windermere.

Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).

In ZIP 34786 (Windermere), 784 homes closed in the last 12 months at a median of $622K ($262/sq ft), down 1.5% year over year, with a median 38 days on market. Right now 113 active and 37 pending listings put supply at about 3.0 months — a balanced market. See the live ZIP 34786 housing market and the Orange County market.

ZIP and county figures describe the wider market, not Windermere Oaks specifically. Momentum Research analysis of MLS records.

Windermere as a town is closely associated with its lakes and equestrian-adjacent lots, and many of its named communities lean on that geography rather than on constructed amenities. Windermere Oaks appears to follow that pattern — the current listing data doesn't surface a pool, gate, or clubhouse tied to the name, which suggests either a smaller subdivision or one where amenities, if any, are informal or shared with a broader area rather than exclusive to this community.

For due diligence purposes, that absence is itself the finding: don't assume HOA-maintained amenities exist here. Any buyer should confirm directly whether an HOA applies, what it covers, and whether nearby lake access or recreation is public, private, or simply not part of the deed. Treat this as a name on a plat map first, and verify the rest property by property.

When a community doesn't have a clean amenity story in the data, the value of a local agent goes up, not down. We verify what's actually attached to a given address — HOA status, deed restrictions, lake or lot specifics — rather than relying on a generic community profile, and we make sure your offer or your listing reflects the property itself, not an assumed package of amenities that may not exist.

Listings in this community report association dues of about $333 per month ($3,996 a year) — the median AssociationFee across 6 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.

Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.